US6046045A - Methods for decomposing quinolones and naphthyridones - Google Patents

Methods for decomposing quinolones and naphthyridones Download PDF

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Publication number
US6046045A
US6046045A US09/051,819 US5181998A US6046045A US 6046045 A US6046045 A US 6046045A US 5181998 A US5181998 A US 5181998A US 6046045 A US6046045 A US 6046045A
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United States
Prior art keywords
rot fungi
dsm
represents hydrogen
compounds
wood
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Expired - Fee Related
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US09/051,819
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English (en)
Inventor
Heinz-Georg Wetzstein
Hans-Georg Rast
Wolfgang Karl
Rainer Martens
Frantisek Zadrazil
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Bayer AG
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Bayer AG
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Priority claimed from DE19617283A external-priority patent/DE19617283A1/de
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Assigned to BAYER AKTIENGESELLSCHAFT reassignment BAYER AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MARTENS, RAINER, ZADRAZIL, FRANTISEK, WETZSTEIN, HEINZ-GEORG, KARL, WOLFGANG, RAST, HANS-GEORG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F3/00—Biological treatment of water, waste water, or sewage
    • C02F3/34—Biological treatment of water, waste water, or sewage characterised by the microorganisms used
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/02—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by biological methods, i.e. processes using enzymes or microorganisms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B09—DISPOSAL OF SOLID WASTE; RECLAMATION OF CONTAMINATED SOIL
    • B09C—RECLAMATION OF CONTAMINATED SOIL
    • B09C1/00—Reclamation of contaminated soil
    • B09C1/10—Reclamation of contaminated soil microbiologically, biologically or by using enzymes
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20—Organic substances
    • A62D2101/22—Organic substances containing halogen
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20—Organic substances
    • A62D2101/28—Organic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen

Definitions

  • the present invention relates to two processes for the degradation of antimicrobially, in particular antibacterially, acting quinolone- and naphthyridonecarboxylic acids and derivatives thereof with the aid of wood rot fungi.
  • Antimicrobially acting substances are widely used in medicine and veterinary medicine.
  • the preparation of these active compounds is accompanied by problems in the elimination of production residues, wastewaters and packaging containing the active compound.
  • the antimicrobial activity of the active compounds can prevent the customary degradation by bacteria in soils, waters and sewage treatment plants.
  • an undesirable interference for example in biologically operating sewage treatment plants, may even occur if relatively large quantities of wastewaters containing active compound have to be processed, i.e. in all these cases an expensive pretreatment of the wastewaters, residues and the like is necessary.
  • EP 0 192 237 A1 mentions some examples of chlorinated hydrocarbons which can be degraded by the white rot fungus Phanerochaete chrysosporium.
  • the present invention relates to:
  • a process for the treatment of wastewaters which comprise antibacterially and antimicrobially acting quinolone- and naphthyridonecarboxylic acids and derivatives thereof with wood rot fungi, in particular white or brown rot fungi.
  • a process for the treatment of manure from intensive animal husbandry which comprises antibacterially and antimicrobially acting quinolone- and naphthyridonecarboxylic acids and derivatives thereof with wood rot fungi, in particular white or brown rot fungi.
  • a process for the treatment of soils which comprise antibacterially and antimicrobially acting quinolone- and naphthyridonecarboxylic acids and derivatives thereof with wood rot fungi, in particular white or brown rot fungi.
  • the best known wood-destroying Basidiomycetes are divided into 2 large groups: on the one hand into the lignin-degrading white rot fungi, and on the other hand into the cellulose- and hemicellulose-degrading brown rot fungi, which essentially do not degrade lignin but merely modify it by hydroxylation and demethylations.
  • White rot fungi are distinguished by extracellular enzymes, such as lignin peroxidases, manganese peroxidases and laccases, which as a rule are missing from brown rot fungi.
  • the two groups can be distinguished by chemical detection methods (cf., for example, Stalpers, 1978, Studies in Mycology, No.
  • Wood rot fungi are known. The abovementioned species of wood rot fungi are included in public collections of microorganisms and are freely accessible; for example, those marked DSM are accessible from the Deutsche Sammlung fur Mikroorganismen [German Collection of Microorganisms] (DSMZ), Mascheroder Weg 1b, 38116 Braunschweig.
  • Antibacterially and antimicrobially acting quinolone- and naphthyridonecarboxylic acids which may be mentioned are the compounds of the following formulae (I) and (II) ##STR1## in which
  • X 1 and X 2 independently of one another represent hydrogen, halogen, C 1-4 -alkyl, C 1-4 -alkoxy or NH 2 ,
  • Y represents radicals of the structures ##STR2## wherein
  • R 16 H, --CH 3 , --CH ⁇ CH--CO 2 R 16' , --CH 2 --CH 2 --CO 2 R 16' , --CH 2 --CO--CH 3 , --CH 2 --CH 2 --CN,
  • R 4 represents hydrogen, optionally hydroxyl- or methoxy-substituted straight-chain or branched C 1 -C 4 -alkyl, cyclo-propyl or acyl having 1 to 3 C atoms,
  • R 5 represents hydrogen, methyl, phenyl, thienyl or pyridyl
  • R 6 represents hydrogen or C 1-4 -alkyl
  • R 7 represents hydrogen or C 1-4 -alkyl
  • R 8 represents hydrogen or C 1-4 -alkyl
  • R 9 represents hydrogen, methyl or --CH 2 --NR 7 R 8 ,
  • R 10 represents hydrogen, C 1-4 -alkyl, amino, optionally hydroxyl-substituted alkyl- or dialkylamino having 1 or 2 C atoms in the alkyl part, amino-C 1-4 -alkyl, C 1-4 -alkylamino-C 1-4 -alkyl or 1-imidazolyl,
  • R 11 represents hydrogen, hydroxyl, methoxy, methylthio, halogen, methyl or hydroxymethyl
  • R 12 represents hydrogen or methyl
  • R 13 represents hydrogen or C 1-4 -alkyl
  • R 14 represents hydrogen or C 1-4 -alkyl
  • R 15 represents hydrogen or C 1-4 -alkyl
  • R 1 represents hydrogen, an optionally halogen-substituted alkyl residue having 1 to 3 carbon atoms, cyclopropyl, methoxy, 4-fluorophenyl, 2,4-difluorophenyl or methylamino,
  • R 2 represents hydrogen or optionally methoxy- or 2-methoxyethoxy-substituted alkyl having 1 to 6 carbon atoms, as well as cyclohexyl, benzyl, 2-oxopropyl, phenacyl, ethoxycarbonylmethyl or pivaloyloxymethyl,
  • R 3 represents hydrogen, methyl or ethyl
  • X 1 and Y together with the adjacent C atoms, represent a dioxolanyl residue or dioxoamyl residue
  • A represents nitrogen or ⁇ CH--, ⁇ C(halogen)--, ⁇ C(OCH 3 )--, ⁇ C(CH 3 )-- or ⁇ C(CN)--,
  • B represents oxygen, optionally methyl- or phenyl-substituted ⁇ N-- as well as ⁇ CH 2 ,
  • Z represents ⁇ CH-- or ⁇ N--
  • the compounds of the formulae I and II can be present in the form of their racemates or in enantiomeric forms.
  • Preferred compounds of the formulae (I) and (II) are those in which
  • R 1 represents optionally fluorine-substituted C 1 -C 3 -alkyl, or represents cyclo-propyl
  • R 1 represents an alkyl residue having 1 to 3 carbon atoms, cyclopropyl, 2-fluoroethyl, methoxy, 4-fluorophenyl, 2,4-difluorophenyl or methylamino,
  • R 2 represents hydrogen or optionally methoxy- or 2-methoxyethoxy- substituted alkyl having 1 to 6 carbon atoms as well as cyclohexyl, benzyl, 2-oxopropyl, phenacyl, ethoxycarbonylmethyl or pivaloyloxymethyl,
  • R 3 represents hydrogen, methyl or ethyl
  • A represents nitrogen or ⁇ CH--, ⁇ C(halogen)--, ⁇ C(OCH 3 )--, ⁇ C(CH 3 )-- or ⁇ C(CN)--,
  • B represents oxygen, optionally methyl- or phenyl-substituted ⁇ N-- as well as ⁇ CH 2 and
  • Z represents ⁇ CH-- or ⁇ N--
  • X 1 and X 2 independently of one another represent hydrogen, halogen or NH 2 ,
  • R 4 represents hydrogen, optionally hydroxyl-substituted straight-chain or branched C 1 -C 3 -alkyl or oxyalkyl having 1 to 4 C atoms,
  • R 5 represents hydrogen, methyl or phenyl
  • R 6 represents hydrogen or methyl
  • R 7 represents hydrogen or methyl
  • R 9 represents hydrogen, methyl or --CH 2 --NH 2 ,
  • R 10 represents hydrogen, methyl, amino, methylamino, dimethylamino, aminomethyl, methylaminomethyl or ethylaminomethyl,
  • R 11 represents hydrogen, hydroxyl, methyl, fluorine, methyl or hydroxymethyl
  • R 13 represents hydrogen or methyl
  • R 14 represents hydrogen or methyl
  • R 15 represents hydrogen or methyl
  • Particularly preferred compounds of the formula (I) are those in which
  • R 1 represents an alkyl radical having 1 to 3 carbon atoms, cyclopropyl, 2-fluoroethyl, methoxy, 2,4-difluorophenyl or methylamino,
  • R 2 represents hydrogen or optionally methoxy- or 2-methoxyethoxy- substituted alkyl having 1 to 6 carbon atoms, as well as cyclohexyl, benzyl, 2-oxopropyl, phenacyl, ethoxycarbonylmethyl or pivaloyloxymethyl,
  • A represents nitrogen or ⁇ CH--, ⁇ C(halogen)--, ⁇ C(CH 3 )--, ⁇ C(OCH 3 )-- or ⁇ C(CN)--,
  • X 1 and X 2 independently of one another represent hydrogen, fluorine or NH 2 ,
  • Y represents radicals of the structures ##STR4## wherein
  • R 16 H or --CH 3 ,
  • R 4 represents hydrogen, optionally hydroxyl-substituted straight-chain or branched C 1 -C 3 -alkyl or hydroxyalkyl having 1 to 4 C atoms,
  • R 5 represents hydrogen, methyl or phenyl
  • R 6 represents hydrogen or methyl
  • R 7 represents hydrogen or methyl
  • R 9 represents hydrogen, methyl or --CH 2 NH 2 ,
  • R 10 represents hydrogen, methyl, amino, methylamino, dimethylamino, aminomethyl, methylaminomethyl or ethylaminomethyl,
  • R 11 represents hydrogen, hydroxyl, methyl, fluorine, methyl or hydroxymethyl
  • R 13 represents hydrogen or methyl
  • R 14 represents hydrogen or methyl
  • R 15 represents hydrogen or methyl
  • Active compounds which may be mentioned as especially preferred are those with the common names enrofloxacin, ciprofloxacin, danofloxacin, ofloxacin, norfloxacin, benofloxacin, sarafloxacin, difloxacin, orbifloxacin, marbofloxacin and oxolinic acid.
  • Active compounds which may be mentioned in particular are enrofloxacin, ciprofloxacin, marbofloxacin, ofloxacin, norfloxacin and oxolinic acid.
  • the process according to the invention is preferably carried out in liquid, solid or semi-solid homogeneous or heterogeneous media.
  • these comprise lignin-, lignocellulose- and/or cellulose-containing material. This includes straw, chaff, wood, wood chips, sawdust and ground cereal residue.
  • malt broth which comprises malt extract or an equivalent source of carbon and energy in a concentration of 1-50 g/l, preferably 5-30 g/l, in particular 5-8 g/l,
  • a rinsing water for example from the preparation process for a quinolone-containing medicament, having a content of 0.01 to 500 ppm, preferably 0.1 to 50 ppm, in particular 1 to 20 ppm, of the quinolone in a ratio of 0.01 to 100 g of dry weight DW/1, preferably 0.1 to 10 g of DW/1, in particular 1 to 3 g of DW/1.
  • the pH of the suspension can be 3 to 8, preferably 4 to 7, in particular 5 to 6; phosphate is not added.
  • Organic acids such as, for example, acetic acid or oxalic acid, can be used to adjust the pH.
  • the content of iron 2+ or iron 3+ should be 0.1 to 100 ⁇ M (10 -6 mol per liter), preferably 1 to 30 ⁇ M, in particular 2 to 20 ⁇ M, the content of NH 4 + can be 0.001 to 20 mM (10 -3 mol per liter), preferably 0.1 to 10 mM, in particular between 0.1 and 1 mM.
  • the content of divalent cations should be between 0.1 and 10 mM, preferably 1 mM (for example 0.2 mM CaCl 2 +0.8 mM MgSO 4 ).
  • This suspension is incubated under the same conditions as the preculture.
  • coniferyl or veratryl alcohol in a concentration of 0.01 to 10 mM, preferably 0.1 to 3 mM, in particular 0.5 to 1 mM, results in an increase in the degrading activity for the quinolone.
  • lignocellulose-containing substances in particular straw, sawdust or wood chips, are inoculated with agar blocks punched out of the stock culture, 0.1 to 100 g of agar per kg of solid substrate, preferably 1 to 10 g of agar per kg of substrate, being employed.
  • water is added to the solid matrix (straw, manure, soil, sludge) comprising the quinolone (0.1 to 200 ppm) until a water content of 10 to 90%, preferably 40 to 50% (based on the weight), is reached.
  • the inoculum is distributed in the solid matrix.
  • the subsequent incubation is carried out at 5 to 40° C., preferably 15 to 30° C., in particular at 18 to 22° C.
  • One liter of rinsing water from a formulating tank having a content of 10 ppm of enrofloxacin is inoculated with a preculture of Gloeophyllum striatum DSM 9592 or Gloeophyllum striatum DSM 10335, during which the fungus mycelium is to be transferred from the preculture in 1/4 concentrated malt broth into the rinsing water such that a concentration of 2 g of dry weight per liter is achieved.
  • This suspension is incubated at room temperature while shaking at 100 rpm in the dark. After 2 weeks, 10 to 20% of the [carbonyl- 14 C]-enrofloxacin employed was degraded to 14 CO 2 .
  • the inoculum comprises 20 agar blocks each weighing about 0.5 g. These small blocks were punched out of a preculture from the fungal colony on malt agar in a Petri dish. The batch was incubated at room temperature in the dark while gassing with moistened air. After 8 weeks, 50% of the enrofloxacin was degraded.
  • 0.1 kg of wheat straw was moistened with 100 ml of water and inoculated with Gloeophyllum striatum DSM 9594. After preincubation for 7 days at room temperature, the straw was covered with a layer of 0.6 kg of field soil (with a water content of about 50%) comprising 10 ppm of enrofloxacin and was incubated at room temperature. After 15 weeks, 6% of the enrofloxacin employed was degraded.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Biomedical Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Mycology (AREA)
  • Biochemistry (AREA)
  • Toxicology (AREA)
  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Business, Economics & Management (AREA)
  • Emergency Management (AREA)
  • Soil Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Processing Of Solid Wastes (AREA)
  • Purification Treatments By Anaerobic Or Anaerobic And Aerobic Bacteria Or Animals (AREA)
  • Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
US09/051,819 1995-10-24 1996-10-11 Methods for decomposing quinolones and naphthyridones Expired - Fee Related US6046045A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19539445 1995-10-24
DE19539445 1995-10-24
DE19617283 1996-04-30
DE19617283A DE19617283A1 (de) 1995-10-24 1996-04-30 Verfahren zum Abbau von Chinolonen und Naphthyridonen
PCT/EP1996/004421 WO1997015354A1 (de) 1995-10-24 1996-10-11 Verfahren zum abbau von chinolonen und naphthyridonen

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US (1) US6046045A (de)
EP (1) EP0858357B1 (de)
JP (1) JPH11514274A (de)
CN (1) CN1200678A (de)
AT (1) ATE180983T1 (de)
AU (1) AU7290296A (de)
ES (1) ES2135254T3 (de)
HU (1) HU221662B1 (de)
WO (1) WO1997015354A1 (de)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6383800B1 (en) * 2000-03-31 2002-05-07 The United States Of America As Represented By The Secretary Of Agriculture Fungal degradation and bioremediation system for pentachlorophenol-treated wood
US6387691B1 (en) * 2000-03-31 2002-05-14 The United States Of America As Represented By The Secretary Of Agriculture Fungal degradation and bioremediation system for ACQ-treated wood
WO2004013322A3 (en) * 2002-08-02 2004-07-29 Klenzyme Ltd Degrading lignocellulosic materials
US20040219652A1 (en) * 2002-03-19 2004-11-04 Covington Anthony Dale Removing deposits of animal dung
US6923912B1 (en) * 2003-07-30 2005-08-02 Sorce, Inc. Method of wastewater treatment utilizing white rot and brown rot fungi
EP1679287A1 (de) * 2005-01-05 2006-07-12 Sorce, Inc. Verfahren zur Abwasserbehandlung unter Verwendung von Weiss- und Braunfäulepilzen
US20080264858A1 (en) * 2001-02-20 2008-10-30 Paul Edward Stamets Delivery systems for mycotechnologies, mycofiltration and mycoremediation
CN110656053A (zh) * 2019-11-01 2020-01-07 广东省微生物研究所（广东省微生物分析检测中心） 一种鳞伞属新菌种及其人工栽培方法和用途

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7444200A (en) * 1999-09-24 2001-04-24 Idemitsu Kosan Co. Ltd Method for decomposing refractory hazardous substance and decomposing agent
US8414748B2 (en) 2003-06-10 2013-04-09 Scimist, Inc. Apparatus and process for mediated electrochemical oxidation of materials
CN106929442B (zh) * 2017-02-24 2020-05-08 暨南大学 一株喹诺酮类抗生素降解菌及其应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0192237A1 (de) * 1985-02-19 1986-08-27 Utah State University Foundation Verfahren zur Absetzung von in der Umwelt beständigen organischen Verbindungen
US5143828A (en) * 1991-12-31 1992-09-01 The United States Of America As Represented By The Secretary Of The Army Method for synthesizing an enzyme-catalyzed polymerized monolayer
DE4314352A1 (de) * 1993-04-30 1994-11-03 Reinhold & Mahle Ag Verfahren zum Abbau ringförmiger kohlenstoffhaltiger Verbindungen

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5143827A (en) * 1989-01-19 1992-09-01 Southern Pacific Petroleum Process for biotechnological upgrading of shale oil
DE4104624C1 (en) * 1991-02-15 1993-01-21 Reko Gmbh Entsorgung Und Recycling, 7123 Sachsenheim, De Degradation of harmful organic material - using lignin-degrading organisms, without the need for specially prepd. substrate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0192237A1 (de) * 1985-02-19 1986-08-27 Utah State University Foundation Verfahren zur Absetzung von in der Umwelt beständigen organischen Verbindungen
US5143828A (en) * 1991-12-31 1992-09-01 The United States Of America As Represented By The Secretary Of The Army Method for synthesizing an enzyme-catalyzed polymerized monolayer
DE4314352A1 (de) * 1993-04-30 1994-11-03 Reinhold & Mahle Ag Verfahren zum Abbau ringförmiger kohlenstoffhaltiger Verbindungen

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6383800B1 (en) * 2000-03-31 2002-05-07 The United States Of America As Represented By The Secretary Of Agriculture Fungal degradation and bioremediation system for pentachlorophenol-treated wood
US6387691B1 (en) * 2000-03-31 2002-05-14 The United States Of America As Represented By The Secretary Of Agriculture Fungal degradation and bioremediation system for ACQ-treated wood
US20080264858A1 (en) * 2001-02-20 2008-10-30 Paul Edward Stamets Delivery systems for mycotechnologies, mycofiltration and mycoremediation
US20040219652A1 (en) * 2002-03-19 2004-11-04 Covington Anthony Dale Removing deposits of animal dung
WO2004013322A3 (en) * 2002-08-02 2004-07-29 Klenzyme Ltd Degrading lignocellulosic materials
US6923912B1 (en) * 2003-07-30 2005-08-02 Sorce, Inc. Method of wastewater treatment utilizing white rot and brown rot fungi
EP1679287A1 (de) * 2005-01-05 2006-07-12 Sorce, Inc. Verfahren zur Abwasserbehandlung unter Verwendung von Weiss- und Braunfäulepilzen
CN110656053A (zh) * 2019-11-01 2020-01-07 广东省微生物研究所（广东省微生物分析检测中心） 一种鳞伞属新菌种及其人工栽培方法和用途
CN110656053B (zh) * 2019-11-01 2021-04-13 广东省微生物研究所（广东省微生物分析检测中心） 一种鳞伞属新菌种及其人工栽培方法和用途

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EP0858357B1 (de) 1999-06-09
JPH11514274A (ja) 1999-12-07
WO1997015354A1 (de) 1997-05-01
HUP9802982A2 (hu) 1999-04-28
CN1200678A (zh) 1998-12-02
EP0858357A1 (de) 1998-08-19
HUP9802982A3 (en) 1999-05-28
AU7290296A (en) 1997-05-15
ATE180983T1 (de) 1999-06-15
ES2135254T3 (es) 1999-10-16
HU221662B1 (hu) 2002-12-28

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